Siesta Key vacation rentals

We found 6,641 vacation rentals — enter your dates for availability

Discover a selection of 817 homes, 249 apartments, and other vacation rentals in Siesta Key that are perfect for your trip. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, such as WiFi and a pool. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Siesta Key

Showing deals for:Jan 9 - Jan 16
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Siesta Key

Why visit Siesta Key

  • Beautiful Beaches: Siesta Key is renowned for its stunning sandy beaches, perfect for sunbathing and relaxation.
  • Outdoor Activities: Engage in various outdoor adventures, from kayaking to biking along scenic trails.
  • Charming Siesta Key Village: Explore the vibrant village filled with family-friendly activities, shops, and dining options.
  • Tranquil Atmosphere: Experience the peaceful vibes of this tropical paradise ideal for unwinding.
  • Diverse Accommodations: Choose from a variety of vacation rentals, including beachfront homes and cozy condos.

Popular types of accommodation in Siesta Key

Planning a getaway to Siesta Key? Exciting times await as you select the perfect place to stay. Discover a variety of vacation rentals, including houses, condos, and apartments, all designed to enhance your beach experience. Whether you're searching for Siesta Key island rentals or luxurious beach accommodations, we’ve got you covered with options that offer comfort and convenience. Dive into your dream vacation with our Siesta Key vacation rentals.

  • Houses: The top choice among travelers, offering spacious accommodations ideal for families, couples, or groups seeking privacy and comfort.
  • Condos: A popular option providing modern amenities and convenient access to beaches, perfect for those wanting a blend of luxury and relaxation.
  • Apartments: A great value choice, offering flexibility and home-like features for those wanting to experience local life.
  • Villas: Elegant and stylish, these rentals offer upscale living spaces with private amenities, ideal for a luxurious getaway.
  • Cottages: Quaint and charming, these cozy accommodations provide a delightful retreat for a peaceful vacation experience.**

Top attractions in and around Siesta Key

Siesta Key, Florida, is the perfect destination for beach lovers and families seeking outdoor adventures. With stunning beaches, urban parks, and marinas, there's something for everyone to enjoy. Explore the beautiful coastline and engage in various activities that cater to both outdoor enthusiasts and those looking for a city experience. Whether traveling solo, as a family, or with friends, Siesta Key offers a memorable getaway filled with fun and relaxation.

  • Siesta Key Beach: Renowned for its powdery white sand and crystal-clear waters, Siesta Key Beach offers a laid-back atmosphere perfect for sunbathing, swimming, and beach sports. Enjoy stunning sunsets and beach vibes that make it a must-visit destination.
  • St. Armands Circle: A vibrant shopping and dining district, St. Armands Circle features upscale boutiques, art galleries, and a variety of restaurants. Experience the lively city vibes as you stroll through this charming area filled with palm trees and outdoor seating.
  • Marina Jack: This picturesque marina offers boat rentals, dining, and scenic views of the water. Engage in outdoor adventures like fishing or sightseeing cruises while soaking in the beautiful beach vibes and fresh ocean air.

Things to do recommended for couples

Looking for a romantic getaway in Siesta Key? Enjoy a luxurious evening at The Oaks Club, catch a performance at the Beatrice Friedman Symphony Center, or have fun at Evie's Golf Center for a playful round of mini-golf. Each experience is sure to create lasting memories.

Things to do recommended for families

Families can catch a game at Ed Smith Stadium, just 6 miles from Siesta Key, soaking in the sports atmosphere. For a relaxing day, head to the Robert L. Taylor Community Complex, located 7 miles away, offering wellness and leisure activities for all ages.

Things to do recommended for groups

Enjoy a night of culture and entertainment at the Van Wezel Performing Arts Hall, explore the scenic trails of Sarasota BayWalk for some adventure, and shop for unique finds at Gulf Gate Mall, perfect for family fun and group bonding.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Siesta Key

When you’re traveling with a group, family, pets, or planning an extended stay, be sure to set your priorities accordingly when searching. Here are some helpful Vrbo booking tips for you.

  • Traveling to Siesta Key with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Siesta Key with young kids: Traveling with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Siesta Key: For many families, a vacation isn't truly a getaway unless their furry companion is along for the ride. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Siesta Key: If you’re in search of vacation rentals that offer discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Siesta Key

Siesta Key, a tropical paradise, offers the perfect beach getaway with its resplendent sands and friendly atmosphere. Explore the charming Siesta Key Village, where family-friendly activities abound. Enjoy the tranquil vibes of this island destination, ideal for outdoor vacations. With its breathtaking beachfront and relaxing scenery, Siesta Key promises an unforgettable experience for all travelers seeking sun, sand, and serenity.

  • Sarasota: Located approximately 5 miles from Siesta Key, Sarasota is a vibrant city known for its stunning beaches and rich cultural scene. Visitors flock to this area for a unique blend of beach relaxation and urban experiences. The city features a variety of shopping malls and centers, making it a perfect spot for retail therapy. Additionally, Sarasota is home to beautiful landmarks such as family-friendly beaches and charming neighborhoods that evoke a sense of community. Whether you're exploring local art galleries or indulging in fresh seafood at waterfront restaurants, Sarasota offers a delightful mix of activities for travelers of all ages.
  • Siesta Key Village: Nestled around Siesta Key, Siesta Key Village is a lively neighborhood that captures the essence of a beach town. This area is favored by families and beach lovers alike, thanks to its picturesque beaches and recreational spaces. Visitors can stroll through the village, enjoying various shopping options and local eateries that offer a taste of the local cuisine. The nearby urban parks provide perfect spots for picnics and outdoor activities, making it an ideal destination for a fun-filled day at the beach. With a friendly atmosphere and a variety of attractions, Siesta Key Village is a must-visit for anyone vacationing in the region.
  • Lido Key: Situated about 3 miles from Siesta Key, Lido Key is a picturesque island known for its beautiful beaches and family-friendly environment. This charming destination invites travelers to explore its shopping centers and recreational areas, perfect for a day of fun in the sun. Lido Key features stunning beachfront access where visitors can relax or partake in water activities. The local parks also provide ample space for outdoor fun and relaxation. With its serene atmosphere and vibrant attractions, Lido Key is an excellent choice for those looking to experience the best of Florida's coastal living.

Best time to go to Siesta Key

If you're planning a trip to Siesta Key, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in January, March and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyModerately HighSlightly Low
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyAverageAverage
March68.0°F (20.0°C)No Rain (Dry)SunnyModerately HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
May77.7°F (25.4°C)Light RainMostly SunnyAverageAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.9°F (28.3°C)Light RainMostly SunnyModerately HighSlightly High
August83.3°F (28.5°C)Light RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Light RainMostly SunnyAverageSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyModerately LowSlightly Low
November70.7°F (21.5°C)No Rain (Dry)Mostly SunnyModerately LowAverage
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and rental type. We're here to help you find the perfect getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your total booking. Being the planner has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and accumulate OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient area for you to plan new trips, manage your existing plans, or review and organize your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out Trip Boards, simply go to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Island paradise at Siesta Key vacation home rentals

Siesta Beach is regularly hailed on lists of the very best in the United States. It strings along Florida's Treasure Coast, fringing the edge of Siesta Key like a wisp of white cloud that's lapped by a sky-blue sea. But the sands aren't the only draw. This barrier isle is also a fun-loving family hotspot, laden with coffee shops and oyster bars, kayak rentals and turtle sanctuaries. Siesta Key vacation rentals cover all sorts, whether you're after a pad overlooking the waves of the Mexican Gulf or a modern apartment that takes the whole crew.

Attractions near your Siesta Key summer rental

There's no doubt about it – the main attraction of Siesta Key is Siesta Beach. That long stretch of sand so white you might just be tempted to spoon it into your morning coffee is regularly hailed as one of the most beautiful in the whole United States. With its aquamarine waters and undulating dunes, it says, "Move over, California!" You could even bag yourself a Siesta Key vacation rental with views over the shoreline, just to make sure you're the first laying down the towel, come morning.

What to do near Siesta Key vacation rentals

Wobbling on a paddle board or blowing bubbles from a snorkeling tube, whizzing on personal watercraft or carving wakes through the Gulf – all sorts of aqua fun is on the menu in Siesta Key. Home to boating outfitters, big fishing tourers, kitesurfing guides and turtle conservationists, this Floridian island is the place to be if you love making a splash. Dolphin cruises and whale spotting usually top the menu for families. A meeting with bottlenoses and beaked whales is all but guaranteed, between December and February.

Something tropical in Siesta Key

The palms and Caribbean-esque sands of Siesta Key should be a clue to the island's tropical nature. Enjoying year-round warmth and 100s of days of sunshine, there's never really a time when the board shorts and bikinis aren't needed. Loads of people will head down during the US winter. Temperatures average around 62–74 between December and March, and there's hardly any rain at all – you'll get a tan while the snows fall in the Midwest. Summer, from June to September, is the hottest time. It also brings more chance of rain and the occasional tropical storm.

Reefs and resplendent sands along Siesta Key

The whole coast of Siesta Key is a patchwork of cotton-white powder and turquoise seas, and a playground for lovers of the beach. You can laze on the brilliant white sands or snorkel through crystal-clear Gulf waters. Talking of the Gulf, there are coral reefs and multicolored fish waiting just off the shore, not to mention pods of whales and dolphins. You can also encounter rare turtles on the appropriately-named Turtle Beach. Alternatively, book your Siesta Key vacation rentals inland, to kayak through Floridian mangroves and creeks.

Best beaches near Siesta Key vacation homes

The beaches of Siesta Key are its biggest draw. Vacation homes are available near beautiful beaches like Siesta Key Beach, a beach of white quartz sand with clear water, playgrounds, and tennis courts, and Crescent Beach, a wide, sandy beach on the Gulf of Mexico with picturesque views. You’ll also enjoy Sarasota Beach, a quiet beach with calm waters perfect for families.

Transportation to and around Siesta Key

The nearest airport is in Sarasota-Bradenton Intl. Airport (SRQ), located 7.8 mi (12.5 km) from the city center.

Family activities near Siesta Key vacation rentals

Siesta Key is filled with unique attractions for kids of all ages. Vacation rentals are available near places like South Lido County Park, a waterfront park with swimming, kayaking, bird watching, and trails, and Turtle Beach, a sandy beach with a native population of sea turtles. You’ll also like Livingston’s Amusement Center, a colossal family-friendly activity space with go-karts, billiards, and games, as well as a bar for adults.

Frequently asked questions

What is the best area to stay in Siesta Key when booking a vacation rental?
When choosing a vacation rental in Siesta Key, Florida, one of the best areas to consider is Siesta Village. This charming neighborhood offers a vibrant atmosphere with an array of shops, restaurants, and bars, making it easy to enjoy a leisurely stroll. The proximity to Siesta Beach, known for its powdery white sand and stunning sunsets, makes it an ideal spot for beach lovers. You'll find a variety of vacation properties here, ranging from cozy cottages to modern condos, providing ample options for different group sizes and budgets.

Another appealing area is the Crescent Beach section, which is quieter and more residential, superb for those seeking relaxation. This beach is often less crowded than Siesta Beach, allowing for a more tranquil experience while still being close to the action. Guests can enjoy the breathtaking views and easy access to the water, making it a great choice for families or couples. There are numerous vacation rentals available here, providing a unique blend of comfort and proximity to nature.

Lastly, the northern part of Siesta Key, near the North Siesta Key Beach, offers a more laid-back vibe with beautiful scenery and a peaceful atmosphere. This area is ideal for those who wish to escape the hustle and bustle while still being close to attractions like the famous Turtle Beach, known for its shelling opportunities. The variety of vacation rentals in this area caters to those looking for a serene retreat amidst the beauty of Florida's coast.
How much does it cost to rent a vacation home in Siesta Key?
Prices for vacation rentals in Siesta Key vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Siesta Key to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Siesta Key vacation house rentals?
You can find great discounts on house rentals in Siesta Key on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Siesta Key?
For renting a beach house in Siesta Key, Florida, the area around Siesta Beach is a prime choice, known for its powdery white sand and turquoise waters. Many vacation rentals here feature amenities such as private balconies with ocean views, outdoor grills, and easy beach access, making them superb for families or groups looking to enjoy the sun and surf.

The northern part of Siesta Key, near Crescent Beach, offers a more tranquil experience, with properties often showcasing lush landscaping, private pools, and direct beach access. These rentals frequently come equipped with modern kitchens, spacious living areas, and sometimes even complimentary beach gear, ensuring a comfortable stay.

Additionally, the Gulfside area is popular for its proximity to local shops and dining options, providing convenience for travelers. Many homes in this area boast outdoor spaces like patios or decks, ideal for enjoying sunset views or alfresco dining. Find your rental near the beach in Siesta Key.
What is the most popular type of vacation rental accomodation in Siesta Key?
In Siesta Key, condos are the most popular vacation rental option, with around 2,228 available throughout the area. These condos are typically located near the beach, providing easy access to the pristine sands and vibrant local atmosphere. Travelers can expect amenities such as fully equipped kitchens, spacious living areas, and often private balconies or patios where they can enjoy ocean views or sunset vistas.

Vacation houses are also a significant choice, with about 739 options available, ideal for families or larger groups. These homes generally feature multiple bedrooms, full kitchens, outdoor spaces with BBQ grills, and sometimes private pools, making them superb for gatherings after a day at the beach. Additionally, there are around 199 villas and 187 apartments, suiting those looking for a more upscale or intimate experience, while a smaller selection of 24 cottages offers a charming, rustic feel.
Are there any family house rentals in Siesta Key?
In Siesta Key, Florida, there are numerous family-friendly house rentals available—nearly 2,000 options throughout the area. This beautiful seaside locale features homes in neighborhoods such as Siesta Village and the more tranquil Midnight Pass, both of which offer easy access to the stunning Siesta Key Beach, known for its powdery white sand and gentle waves.

Properties in Siesta Village often come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor patios or decks great for barbecues. Many of these homes also include amenities like private pools, game rooms, and laundry facilities, enhancing the comfort for families traveling together.

On the other hand, rentals near Midnight Pass tend to provide a quieter atmosphere, with some offering private beach access and serene views of the surrounding waters. See all family-friendly rentals in Siesta Key.
Can I rent a vacation home with a pool or hot tub in Siesta Key?
In Siesta Key, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 2,883 options to choose from. This beautiful barrier island is renowned for its stunning beaches and laid-back atmosphere, making it a popular destination for travelers.

You can expect a variety of amenities in these properties, including private swimming pools, relaxing hot tubs, and spacious outdoor areas great for sunbathing or entertaining. Many rentals also come with fully equipped kitchens, allowing guests to prepare meals at their leisure, as well as comfortable living spaces to unwind after a day at the beach. Find your rental in Siesta Key with a pool or a hot tub.
Can I find long-stay vacation rentals in Siesta Key?
A long-stay vacation rental in Siesta Key is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Siesta Key?
In Siesta Key, travelers can find a substantial number of pet-friendly house rentals, with around 488 options available. This charming coastal destination is known for its stunning white sandy beaches and vibrant local culture, making it an ideal spot for those looking to vacation with their pets. Many of the house rentals in the area come equipped with desirable amenities such as private pools, outdoor patios, and fully furnished kitchens, ensuring a comfortable stay for both guests and their furry companions.

The area surrounding Siesta Key is dotted with parks and pet-friendly beaches, providing ample opportunities for outdoor activities with pets. Siesta Beach itself allows pets on certain sections, making it a great place for long walks and playtime in the sand. Additionally, nearby parks like Phillippi Estate Park offer scenic walking trails and picnic areas, superb for enjoying a day out with your pet. See all pet-friendly rentals in Siesta Key.
Are there any remote work vacation rentals in Siesta Key?
In Siesta Key, there are numerous vacation rentals that cater to remote work needs, with around 3,045 options available. This idyllic coastal destination offers properties that are well-equipped for professionals looking to balance work and leisure. Many rentals feature dedicated office spaces or desks, high-speed Wi-Fi, and comfortable workstations, allowing for productivity even while on vacation.

The area is known for its stunning beaches, particularly Siesta Beach, famous for its powdery white sand and vibrant sunsets, providing a superb backdrop for relaxation after work. Additionally, the nearby village of Siesta Key boasts charming shops, restaurants, and local attractions, creating a lively atmosphere for downtime. Travelers can expect amenities like fully equipped kitchens, outdoor seating areas, and sometimes even pool access, enhancing the overall experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Siesta Key vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Siesta Key with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Siesta Key?
In Siesta Key, popular rental amenities include WiFi, kitchens, and access to heated pools, with many properties featuring shared pool facilities. These amenities cater to travelers looking for comfort and convenience, allowing them to prepare meals and stay connected while enjoying the beautiful surroundings.
When is the best time to visit Siesta Key for a vacation rental?
The best time to visit Siesta Key for a vacation rental is during the peak season from January to March. This period attracts travelers seeking sunny escapes to enjoy the pristine beaches, vibrant local culture, and a host of outdoor activities. With temperatures typically ranging from the mid-60s to the mid-70s Fahrenheit, you can comfortably spend your days lounging on the world-famous Siesta Beach or exploring the nearby nature trails.

January stands out as a popular month, providing a superb blend of mild winter weather and an engaging atmosphere. Visitors can partake in a variety of water sports, from paddleboarding to kayaking, while also enjoying the lively local events and festivals that often take place during this time.

For those looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, with fewer tourists and the added bonus of beautiful weather, ideal for beach walks and exploring the charming shops and restaurants without the crowds.
How early should I book a Siesta Key vacation rental?
Book your Siesta Key vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Siesta Key?
In Siesta Key, visitors can discover a variety of attractions that highlight the area's natural beauty and vibrant culture. The renowned Siesta Beach, famous for its powdery white sand, offers a great spot for sunbathing and swimming. Nearby, the Siesta Key Village features charming shops, restaurants, and nightlife options, making it a lively hub for both relaxation and entertainment.

For nature enthusiasts, the nearby Turtle Beach provides a more secluded experience with opportunities for kayaking and fishing. The area's beautiful sunsets can be enjoyed from the public beach accesses or waterfront dining spots.
Can I change or cancel my Siesta Key home rental booking on Vrbo?
To find Siesta Key vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Siesta Key vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Vacation Ideas